Composition containing a polyol and a reaction product

ABSTRACT

The invention relates to a composition comprising at least one hyperbranched polyol having at least two hydroxyl groups and at least one reaction product of at least one oil-soluble high carbon polar modified polymer and at least one polyamine.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims the benefit of priority from U.S. ProvisionalApplication Ser. No. 61/221,388, filed Jun. 29, 2009, the entirecontents of which are hereby incorporated by reference.

FIELD OF THE INVENTION

The present invention relates to compositions comprising at least onepolyol having at least two hydroxyl groups and at least one reactionproduct of at least one oil-soluble high carbon polar modified polymerand at least one polyamine. The reaction product can act as a carrier ormatrix for desired agents. Such compositions have industrial,pharmacological and/or cosmetic applicability.

DISCUSSION OF THE BACKGROUND

U.S. Pat. No. 6,492,455 discloses water-soluble reaction products ofpolyamines and C6 olefin/maleic anhydride copolymers. Because thesecompositions are water-soluble, addition of water to such reactionproducts renders the products unsuitable for applications requiringwater-insolubility. For example, such reaction products are unsuitablefor use as a solid carrier containing colorant (for example, industrialpigments) or active agents (for example, pharmaceuticals) because thereaction product breaks down upon exposure to water.

Thus, there remains a need for improved products which can function as acarrier and/or matrix for desired agents.

SUMMARY OF THE INVENTION

The present invention relates to compositions comprising at least onepolyol having at least two hydroxyl groups and at least one reactionproduct of at least one oil-soluble high carbon polar modified polymerand at least one polyamine.

The present invention also relates to compositions comprising at leastone polyol having at least two hydroxyl groups, at least one reactionproduct of at least one oil-soluble high carbon polar modified polymerand at least one polyamine, and a desired agent such as a colorant orpharmacologically active agent.

The present invention also relates to compositions comprising at leastone polyol having at least two hydroxyl groups, at least one reactionproduct of at least one oil-soluble high carbon polar modified polymerand at least one polyamine, and water. Preferably, such compositions aresolid and/or further comprise a desired agent.

The present invention also relates to compositions comprising at leastone polyol having at least two hydroxyl groups, at least one reactionproduct of at least one oil-soluble high carbon polar modified polymerand at least one polyamine, and at least one oil. Preferably, suchcompositions are solid and/or further comprise a desired agent.

The present invention further relates to cosmetic compositionscomprising at least one polyol having at least two hydroxyl groups andat least one reaction product of at least one oil-soluble high carbonpolar modified polymer and at least one polyamine.

The present invention also relates to methods of treating, caring forand/or making up keratinous material (for example, skin, eyes, eyelashesor lips) by applying cosmetic compositions of the present invention tothe keratinous material in an amount sufficient to treat, care forand/or make up the keratinous material.

The present invention also relates to methods of improving the feel ortexture properties of a cosmetic composition upon application to akeratin material, and/or the adhesion, long-wear and/ortransfer-resistance properties of a cosmetic composition, comprisingadding to and/or forming within a composition a reaction product of atleast one polyamine and at least one oil-soluble high carbon polarmodified polymer, wherein the composition further comprises at least onepolyol having at least two hydroxyl groups.

It is to be understood that both the foregoing general description andthe following detailed description are exemplary and explanatory only,and are not restrictive of the invention.

DETAILED DESCRIPTION OF THE INVENTION

As used herein, the expression “at least one” means one or more and thusincludes individual components as well as mixtures/combinations.

Other than in the operating examples, or where otherwise indicated, allnumbers expressing quantities of ingredients and/or reaction conditionsare to be understood as being modified in all instances by the term“about,” meaning within 10% to 15% of the indicated number.

“Film former” or “film forming agent” as used herein means a polymer orresin that leaves a film on the substrate to which it is applied, forexample, after a solvent accompanying the film former has evaporated,absorbed into and/or dissipated on the substrate.

“Transfer resistance” as used herein refers to the quality exhibited bycompositions that are not readily removed by contact with anothermaterial, such as, for example, a glass, an item of clothing or theskin, for example, when eating or drinking. Transfer resistance may beevaluated by any method known in the art for evaluating such. Forexample, transfer resistance of a composition may be evaluated by a“kiss” test. The “kiss” test may involve application of the compositionto human keratin material such as hair, skin or lips followed by rubbinga material, for example, a sheet of paper, against the hair, skin orlips after expiration of a certain amount of time following application,such as 2 minutes after application. Similarly, transfer resistance of acomposition may be evaluated by the amount of product transferred from awearer to any other substrate, such as transfer from the hair, skin orlips of an individual to a collar when putting on clothing after theexpiration of a certain amount of time following application of thecomposition to the hair, skin or lips. The amount of compositiontransferred to the substrate (e.g., collar, or paper) may then beevaluated and compared. For example, a composition may be transferresistant if a majority of the product is left on the wearer's hair,skin or lips. Further, the amount transferred may be compared with thattransferred by other compositions, such as commercially availablecompositions. In a preferred embodiment of the present invention, littleor no composition is transferred to the substrate from the hair, skin orlips.

“Long wear” compositions as used herein, refers to compositions wherecolor remains the same or substantially the same as at the time ofapplication, as viewed by the naked eye, after an extended period oftime. Long wear properties may be evaluated by any method known in theart for evaluating such properties. For example, long wear may beevaluated by a test involving the application of a composition to humanhair, skin or lips and evaluating the color of the composition after anextended period of time. For example, the color of a composition may beevaluated immediately following application to hair, skin or lips andthese characteristics may then be re-evaluated and compared after acertain amount of time. Further, these characteristics may be evaluatedwith respect to other compositions, such as commercially availablecompositions.

“Tackiness” as used herein refers to the adhesion between twosubstances. For example, the more tackiness there is between twosubstances, the more adhesion there is between the substances. Toquantify “tackiness,” it is useful to determine the “work of adhesion”as defined by IUPAC associated with the two substances. Generallyspeaking, the work of adhesion measures the amount of work necessary toseparate two substances. Thus, the greater the work of adhesionassociated with two substances, the greater the adhesion there isbetween the substances, meaning the greater the tackiness is between thetwo substances.

Work of adhesion and, thus, tackiness, can be quantified usingacceptable techniques and methods generally used to measure adhesion,and is typically reported in units of force time (for example, gramseconds (“g s”)). For example, the TA-XT2 from Stable Micro Systems,Ltd. can be used to determine adhesion following the procedures setforth in the TA-XT2 Application Study (ref: MATI/PO.25), revised January2000, the entire contents of which are hereby incorporated by reference.According to this method, desirable values for work of adhesion forsubstantially non-tacky substances include less than about 0.5 g s, lessthan about 0.4 g s, less than about 0.3 g s and less than about 0.2 g s.As known in the art, other similar methods can be used on other similaranalytical devices to determine adhesion.

“Waterproof” as used herein refers to the ability to repel water andpermanence with respect to water. Waterproof properties may be evaluatedby any method known in the art for evaluating such properties. Forexample, a mascara composition may be applied to false eyelashes, whichmay then be placed in water for a certain amount of time, such as, forexample, 20 minutes. Upon expiration of the pre-ascertained amount oftime, the false eyelashes may be removed from the water and passed overa material, such as, for example, a sheet of paper. The extent ofresidue left on the material may then be evaluated and compared withother compositions, such as, for example, commercially availablecompositions. Similarly, for example, a composition may be applied toskin, and the skin may be submerged in water for a certain amount oftime. The amount of composition remaining on the skin after thepre-ascertained amount of time may then be evaluated and compared. Forexample, a composition may be waterproof if a majority of the product isleft on the wearer, e.g., eyelashes, skin, etc. In a preferredembodiment of the present invention, little or no composition istransferred from the wearer.

“Substituted” as used herein, means comprising at least one substituent.Non-limiting examples of substituents include atoms, such as oxygenatoms and nitrogen atoms, as well as functional groups, such as hydroxylgroups, ether groups, alkoxy groups, acyloxyalkyl groups, oxyalkylenegroups, polyoxyalkylene groups, carboxylic acid groups, amine groups,acylamino groups, amide groups, halogen containing groups, ester groups,thiol groups, sulphonate groups, thiosulphate groups, siloxane groups,and polysiloxane groups. The substituent(s) may be further substituted.

“Volatile”, as used herein, means having a flash point of less thanabout 100° C.

“Non-volatile”, as used herein, means having a flash point of greaterthan about 100° C.

The compositions and methods of the present invention can comprise,consist of, or consist essentially of the essential elements andlimitations of the invention described herein, as well as any additionalor optional ingredients, components, or limitations described herein orotherwise useful.

In accordance with the present invention, the “hardness” of thecomposition may also be considered. The hardness of a composition may,for example, be expressed in gramforce (gf). The composition of thepresent invention may, for example, have a hardness ranging from 20 gfto 2000 gf, such as from 20 gf to 900 gf, and further such as from 20 gfto 600 gf, including all ranges and subranges therebetween.

This hardness is measured in one of two ways. A first test for hardnessis according to a method of penetrating a probe into the composition andin particular using a texture analyzer (for example TA-XT2i from Rheo)equipped with an ebonite cylinder of height 25 mm and diameter 8 mm. Thehardness measurement is carried out at 20° C. at the center of 5 samplesof the composition. The cylinder is introduced into each sample ofcomposition at a pre-speed of 2 mm/s and then at a speed of 0.5 mm/s andfinally at a post-speed of 2 mm/s, the total displacement being 1 mm.The recorded hardness value is that of the maximum peak observed. Themeasurement error is ±50 gf.

The second test for hardness is the “cheese wire” method, which involvescutting an 8.1 mm or preferably 12.7 mm in diameter stick compositionand measuring its hardness at 20° C. using a DFGHS 2 tensile testingmachine from Indelco-Chatillon Co. at a speed of 100 mm/minute. Thehardness value from this method is expressed in grams as the shear forcerequired to cut a stick under the above conditions. According to thismethod, the hardness of compositions according to the present inventionwhich may be in stick form may, for example, range from 30 gf to 300 gf,such as from 30 gf to 250 gf, for a sample of 8.1 mm in diameter stick,and further such as from 30 gf to 200 gf, and also further such as from30 gf to 120 gf for a sample of 12.7 mm in diameter stick.

The skilled artisan may choose to evaluate a composition using at leastone of the tests for hardness outlined above based on the applicationenvisaged and the hardness desired. If one obtains an acceptablehardness value, in view of the intended application, from at least oneof these hardness tests, the composition falls within preferredembodiments of the invention.

Hyperbranched Polyol Compound

According to the present invention, compositions comprising at least onehyperbranched polyol compound are provided. In accordance with thepresent invention, the hyperbranched polyol compound has at least twohydroxyl groups available to react with hydrophilic groups on thebackbone of the polar modified wax.

“Hydroxyl number” or “hydroxyl value” which is sometimes also referredto as “acetyl value” is a number which indicates the extent to which asubstance may be acetylated; it is the number of milligrams of potassiumhydroxide required for neutralization of the acetic acid liberated onsaponifying 1 g of acetylated sample. According to preferredembodiments, the at least one hyperbranched polyol has a hydroxyl numberbetween 50 and 250, preferably between 75 and 225, preferably between100 and 200, preferably between 125 and 175, including all ranges andsubranges therebetween such as 90 to 150.

In accordance with the present invention, “hyperbranched polyol” refersto dendrimers, hyperbranched macromolecules and other dendron-basedarchitectures. Hyperbranched polyols can generally be described asthree-dimensional highly branched molecules having a tree-likestructure. They are characterized by a great number of end groups, atleast two of which are hydroxyl groups. The dendritic or “tree-like”structure preferably shows regular symmetric branching from a centralmultifunctional core molecule leading to a compact globular orquasi-globular structure with a large number of end groups per molecule.Suitable examples of hyperbranched polyols can be found in U.S. Pat. No.7,423,104, and U.S. patent applications 2008/0207871 and 2008/0286152,the entire contents of all of which are hereby incorporated byreference. Other suitable examples include alcohol functional olefinicpolymers such as those available from New Phase Technologies.

Dendrimers tend to be exact, monodisperse structures built layerwise (ingenerations) around a core moiety, with a polymer branching point inevery repeating unit. Hyperbranched polymers tend to possess a number ofcharacteristics which are similar to dendrimers but they tend to bepolydispersed and contain relatively linear segments off of which aplurality of highly branched segments are grown or attached.

Furthermore, “hyperbranched polymers” refers to polymers comprising atleast two, for example three, polymeric branches, forming either themain branch or a secondary branch, and each comprising at least one atleast trifunctional branch point, which may be identical or different,and which is able to form at least two at least trifunctional branchpoints, different from and independent of one another. Each branch pointmay be, for example, arranged in the interior of at least one chain. Thebranches may be, for example, connected to one another by apolyfunctional compound.

As used herein, “trifunctional branch point” means the junction pointbetween three polymer branches, of which at least two branches may bedifferent in chemical constitution and/or structure. For example,certain branches may be hydrophilic, i.e. may predominantly containhydrophilic monomers, and other branches may be hydrophobic, i.e., maypredominantly contain hydrophobic monomers. Further branches mayadditionally form a random polymer or a block polymer.

As used herein, “at least trifunctional branch” means the junctionpoints between at least three polymeric branches, for example npolymeric branches, of which n−1 branches at least are different inchemical constitution and/or structure.

As used herein, “chain interior” means the atoms situated within thepolymeric chain, to the exclusion of the atoms forming the two ends ofthis chain.

As used herein, “main branch” means the branch or polymeric sequencecomprising the greatest percentage by weight of monomer(s).

Branches which are not main branches are called “secondary branches”.

According to particularly preferred embodiments of the presentinvention, the hyperbranched polyol comprises a hydrophobic chaininterior. Preferably, the chain interior comprises one or morehydrocarbon groups, one or more silicon-based groups, or mixturesthereof. Particularly preferred chain interiors comprise olefinicpolymers or copolymers and/or silicone polymers or copolymers.

Suitable olefinic monomers include, but are not limited to, compoundshaving from about 2 to about 30 carbon atoms per molecule and having atleast one olefinic double bond which are acyclic, cyclic, polycyclic,terminal α, internal, linear, branched, substituted, unsubstituted,functionalized, and/or non-functionalized. For example, suitablemonomers include ethylene, propylene, 1-butene, 2-butene,3-methyl-1-butene, and isobutylene.

Suitable silicone groups for inclusion into the interior chain include“D” groups (for example, dimethicone or substituted dimethicone groups).

An exemplary structure is as follows:

Where X corresponds to hydroxyl functionality and R corresponds to amethyl group or an alkyl group preferably containing 2-30 atoms.

According to preferred embodiments, the at least one hyperbranchedpolyol has a molecular weight (Mw) between about 3,000 and 25,000,preferably between 4,000 and 22,000, preferably between 5,000 and20,000, including all ranges and subranges therebetween such as 4000 to5500.

According to preferred embodiments, the at least one hyperbranchedpolyol has a viscosity at 90° F. of between 1,000 and 8,000 centipoise(cps), preferably 2,000 and 7,000 cps, and preferably 3,000 and 6,000cps, including all ranges and subranges therebetween.

According to preferred embodiments, the at least one hyperbranchedpolyol is present in the composition of the present invention in anamount ranging from about 0.1 to about 15% by weight, more preferablyfrom about 1 to about 10% by weight, most preferably from about 2 toabout 8% by weight, based on the total weight of the composition,including all ranges and subranges within these ranges.

Oil-Soluble High Carbon Polar Modified Polymer

According to the present invention, compositions comprising at least oneoil-soluble high carbon polar modified polymer are provided. “Polarmodified polymer” as used herein refers to a hydrophobic homopolymer orcopolymer which has been modified with hydrophilic unit(s).“Oil-soluble” as used herein means that the polar modified polymer issoluble in oil. “High carbon” means more than 20 carbon atoms.

Suitable monomers for the hydrophobic homopolymers and/or copolymersinclude, but are not limited to, cyclic, linear or branched, substitutedor unsubstituted, C22-C40 compounds such as, C22-C28 compounds, C24-C26compounds, C26-C28 compounds, and C30-C38 compounds, including allranges and subranges therebetween. Preferably, the monomers are C24-26compounds, C26-C28 compounds or C30-C38 compounds.

Suitable hydrophilic unit(s) include, but are not limited to, maleicanhydride, acrylates, alkyl acrylates such as, for example, methylacrylate, ethyl acrylate, propyl acrylate, and butyl acrylate, andpolyvinylpyrrolidone (PVP).

According to preferred embodiments, the oil-soluble high carbon polarmodified polymer is a wax. Also preferably, the oil-soluble high carbonpolar modified polymer wax has one or more of the following properties:

a weight-average molecular weight Mw of less than or equal to 30 000g/mol, preferably of 500 to 10 000 g/mol and particularly preferably of1000 to 5,000 g/mol, including all ranges and subranges therebetween;

a number-average molecular weight Mn of less than or equal to 15 000g/mol, preferably of 500 to 12 000 g/mol and particularly preferably of1000 to 5000 g/mol, including all ranges and subranges therebetween;

a molar mass distribution Mw/Mn in the range from 1.5 to 10, preferablyfrom 1.5 to 5, particularly preferably from 1.5 to 3 and especiallypreferably from 2 to 2.5, including all ranges and subrangestherebetween; and/or

a crystallinity of 8% to 60%, preferably 9% to 40%, and more preferably10% to 30%, including all ranges and subranges therebetween, asdetermined by differential scanning calorimetry.

According to preferred embodiments relating to a copolymer wax, it ispreferable to have, based on the total weight of the copolymer backbone,0.1 to 30% by weight of structural units originating from the onemonomer and 70.0 to 99.9% by weight of structural units originating fromthe other monomer.

Waxes of the present invention can be based upon homopolymers orcopolymers made, for example, by the process described in EP 571 882,the entire contents of which is hereby incorporated by reference.Suitable preparation processes include, for example, suspensionpolymerization, solution polymerization and gas-phase polymerization ofolefins in the presence of catalysts, with polymerization in themonomers also being possible.

Oil-soluble high carbon polar modified polymer wax can be produced in aknown manner from the homopolymers and copolymers described above byoxidation with oxygen-containing gases, for example air, or by graftreaction with polar monomers, for example maleic acid or acrylic acid orderivatives of these acids. The polar modification of polyolefin waxesby oxidation with air is described, for example, in EP 0 890 583 A1, andthe modification by grafting is described, for example, in U.S. Pat. No.5,998,547, the entire contents of both of which are hereby incorporatedby reference in their entirety.

Acceptable oil-soluble high carbon polar modified polymer waxes include,but are not limited to, homopolymers and/or copolymers of C24, C25and/or C26 groups, copolymers C26, C27 and/or C28 groups, or copolymersof C30-C38 groups, which have been modified with hydrophilic units suchas, for example, maleic anhydride, acrylate, methacrylate,polyvinylpyrrolidone (PVP), etc. Preferably, the oil-soluble high carbonpolar modified polymer wax has from about 5% to about 30% hydrophilicunits, more preferably from about 10% to about 25% hydrophilic units byweight with respect to the weight of the wax, including all ranges andsubranges therebetween. Particularly preferred hydrophilically modifiedwaxes are C26, C27 and/or C28 homopolymers and copolymers which havebeen modified with maleic anhydride units.

Particularly preferred oil-soluble high carbon polar modified polymerwaxes for use in the present invention are C26-C28 alpha olefin maleicacid anhydride copolymer waxes commercially available from Clariantunder the trade name LICOCARE or LICOCENE. Specific examples of suchwaxes include products marketed by Clariant under the LicoCare namehaving designations such as CM 401, which is a maleic anhydride modifiedwax having a Mw of 2025 and a crystallinity of 11%, C30-C38olefin/isopropylmaleate/maleic anhydride copolymer sold by Baker Hughesunder the name Performa® V 1608, and C24-C26 alpha olefin acrylatecopolymer wax commercially available from Clariant under the trade nameLICOCARE CA301 LP3346 based on a polar backbone with C24-26 side chainswith alternating ester and carboxylic acid groups.

According to other embodiments of the present invention, the polarmodified polymer is not a wax. In accordance with these embodiments ofthe present invention, the polar modified polymer is based upon ahomopolymer and/or copolymer of hydrophobic monomer(s) and has aweight-average molecular weight Mw of less than or equal to 1,000,000g/mol, preferably of 1000 to 250,000 g/mol and particularly preferablyof 5,000 to 50,000 g/mol, including all ranges and subrangestherebetween.

In accordance with these embodiments, the polar modified polymer can beof any form typically associated with polymers such as, for example,block copolymer, a grafted copolymer or an alternating copolymer. Forexample, the polar modified polymer can contain a hydrophobic backbone(such as polypropylene and/or polyethylene) onto which hydrophilicgroups (such as maleic anhydride) have been attached by any meansincluding, for example, grafting. The attached groups can have anyorientation (for example, atactic, isotactic or syndiotactic along thebackbone).

Preferably, the oil-soluble high carbon polar modified polymer(s)represent from about 1% to about 20% of the total weight of thecomposition, more preferably from about 3% to about 17% of the totalweight of the composition, and most preferably from about 5% to about15%, including all ranges and subranges therebetween.

Polyamine Compound

According to the present invention, compositions comprising at least onepolyamine compound are provided. In accordance with the presentinvention, the polyamine compound has at least two primary amine groupsavailable to react with hydrophilic groups of the oil-soluble polarmodified polymer.

According to particularly preferred embodiments, the polyamine compoundis a polyalkyleneamine, preferably a C2-C5 polyalkyleneamine compound,more preferably a polyethyleneimine or polypropyleneimine. Mostpreferably, the polyalkyleneamine is polyethyleneimine (“PEI”). Thepolyalkyleneamine compound preferably has an average molecular weightrange of from 500-200,000, including all ranges and subrangestherebetween.

According to preferred embodiments, compositions of the presentinvention contain polyethyleneimine compounds in the form of branchedpolymers. Commercially available examples of such polymers are availablefrom BASF under the tradename LUPASOL or POLYIMIN. Non-limiting examplesof such polyethyleneimines include Lupasol® PS, Lupasol® PL, Lupasol®PR8515, Lupasol® G20, Lupasol® G35.

According to other embodiments of the present invention, polyamines suchas polyethyleneimines and polypropyleneimines can be in the form ofdendrimers. Non-limiting examples of such dendrimers are manufactured bythe company DSM, and/or are disclosed in U.S. Pat. Nos. 5,530,092 and5,610,268, the contents of which are hereby incorporated by reference.Commercially available examples of such polymers include polyamidoamineor polypropyleneimine polymers from DENDRITECH sold under the STARBURST®name.

According to other embodiments of the present invention, derivatives ofpolyalkyleneamines are suitable polyamines. Such derivatives include,but are not limited to, alkylated derivatives, the addition products ofalkylcarboxylic acids to polyalkyleneamines, the addition products ofketones and of aldehydes to polyalkyleneamines, the addition products ofisocyanates and of isothiocyanates to polyalkyleneamines, the additionproducts of alkylene oxide or of polyalkylene oxide block polymers topolyalkyleneamines, quaternized derivatives of polyalkyleneamines, theaddition products of a silicone to polyalkyleneamines, and copolymers ofdicarboxylic acid and polyalkyleneamines. Even further suitablepolyamines include, but are not limited to, polyvinylimidazoles(homopolymers or copolymers), polyvinylpyridines (homopolymers orcopolymers), compounds comprising vinylimidazole monomers (see, forexample, U.S. Pat. No. 5,677,384, hereby incorporated by reference), andpolymers based on amino acids containing a basic side chain (preferablyselected from proteins and peptides comprising at least 5%, preferablyat least 10% of amino acids selected from histidine, lysine andarginine). Such suitable polyamines as described above include thosedisclosed and described in U.S. Pat. No. 6,162,448, the contents ofwhich are hereby incorporated by reference. Commercially availableexamples of such polymers include polyvinylamine/formamide such as thosesold under the Lupamine® name by BASF, chitosan from vegetable originsuch as those sold under the Kiosmetine® or Kitozyme® names, orcopolymer 845 sold by ISP.

According to preferred embodiments, the at least one polyamine compoundis present in the composition of the present invention in an amountranging from about 0.05 to about 20% by weight, more preferably fromabout 0.2 to about 10% by weight, more preferably from about 0.5 toabout 5% by weight, based on the total weight of the composition,including all ranges and subranges within these ranges.

Preferably, the amount of polyamine compound reacted with theoil-soluble polar modified polymer is such that at least two aminegroups on the polyamine compound react with the oil-soluble polarmodified polymer to form links or bonds between the amine groups and thehydrophilic groups of the oil-soluble polar modified polymer. Theappropriate amount of polyamine compound to react with the oil-solublepolar modified polymer to obtain a reaction product can be easilydetermined, taking into account the number/amount of reactive aminegroups on the polyamine compound and the number/amount of correspondingreactive groups on the oil-soluble polar modified polymer (for example,maleic anhydride groups). According to preferred embodiments, excessoil-soluble polar modified polymer (as determined by the relativenumber/amount of corresponding reactive groups on the polymer ascompared to the reactive amine groups on the polyamine) is reacted withpolyamine. Preferably, the polyamine to oil-soluble polar modified ratiois between 0.005 and 1, preferably between 0.006 and 0.5, and preferablybetween 0.007 and 0.1, including all ranges and subranges therebetween.

Reaction Product

According to preferred embodiments of the present invention, theoil-soluble high carbon polar modified polymer is reacted with thepolyamine compound, in the presence of water in, at minimum, an amountsufficient to solubilize the polyamine, to form a reaction product. Inaccordance with the preferred embodiments, the reaction product iswater-insoluble.

Although not wanting to be bound by any particular theory, it isbelieved that at a temperature below 100° C., the reaction of theoil-soluble high carbon polar modified polymer with the primary aminegroup of the polyamine opens the anhydride ring to form a half acid andhalf amide crosslinked product. However, at a temperature above 100° C.,the reaction of the oil-soluble polar modified polymer with the primaryamine group of the polyamine opens the anhydride ring to form an imidecrosslinked product. The former product is preferred over the latterproduct. It is not necessary for all amine groups and all hydrophilicgroups to react with each other to form the reaction product. Rather, itis possible that the composition may contain free polyamine and/or freeoil-soluble high carbon polar modified polymer in addition to thereaction product.

Although not wanting to be bound by any particular theory, it is alsobelieved that the polyamine(s) can be non-covalently assembled with thepolar modified polymer(s) by electrostatic interaction between an aminegroup of the polyamine and a hydrophilic group (for example, carboxylicacid group associated with maleic anhydride groups) of the polarmodified polymer to form a supramolecule. For example, with specificreference to maleic anhydride groups, in the presence of water thesegroups can open to form dicarboxylic acid groups which can interact withprotonated primary amines of the polyamine through ionic interaction toform a polymer-polymer complex with hydrophilic core crosslinkers and ahydrophobic network that act as supramolecular capsule. If a largeamount of maleic anhydride groups are present, the secondary aminegroups of polyamine are also protonated and interact with alkylcarboxylates.

According to preferred embodiments, the oil-soluble high carbon polarmodified polymer is in an oil carrier, and the polyamine compound is inan aqueous carrier, and the reaction occurs by combining the oil carrierand the aqueous carrier. Because the oil-soluble high carbon polarmodified polymer is typically solid at room temperature, the oil carrieris preferably heated to liquefy the polymer prior to combination withthe aqueous carrier. Preferably, the oil carrier is heated beyond themelting point of the oil-soluble polar modified polymer, typically up toabout 80° C., 90° C. or 100° C.

Without intending to be bound by any particular theory, it is believedthat the reason for this is that due to the chemical and physicalreactions which take place when the oil-soluble polar modified polymeris combined with the polyamine, the subsequent reaction product that isformed is surprisingly and unexpectedly able to entrap large amounts ofwater molecules within its hydrophobic matrix. The resultant product iseminently capable of forming a film, is self-emulsifying, waterproof.Moreover, the product is both stable and capable of carrying varioustypes of ingredients.

Preferably, the amount of polyamine compound reacted with the polarmodified wax is such that virtually all of the at least two amine groupson the polyamine compound react with the polar modified wax such thatvirtually no free amine groups are present on the reaction product. Theexact amount of polyamine compound to react with the polar modified waxto obtain a reaction product having virtually no free amine groups canbe easily determined, taking into account the number/amount of reactiveamine groups on the polyamine compound and the number/amount ofcorresponding reactive groups on the polar modified wax (for example,maleic anhydride groups). According to preferred embodiments, excesspolar modified wax (as determined by the relative number/amount ofcorresponding reactive groups on the wax as compared to the reactiveamine groups on the polyamine) is reacted with polyamine. Preferably,such an excess is at least 2:1, more preferably at least 3:1.

Preferably, when the reaction product is exposed to liquid, the liquidcan be incorporated within the reaction product. Thus, rather thanforming a solution when exposed to liquid, the reaction productpreferably maintains its structure. Preferably, the reaction productforms a matrix or carrier containing the liquid. According to preferredembodiments of the present invention, liquid comprising a desired agentcan be incorporated into the reaction product such that the reactionproduct is a matrix or carrier for the liquid and/or desired agent.

According to preferred embodiments, the reaction product is prepared inthe presence of a catalyst. Using a catalyst in a reaction lasting asufficient amount of time will enable near or full reaction to occur.Any suitable catalyst can be used in the reaction. The exact nature ofthe catalyst will depend upon the nature of the corresponding reactivegroup of the Oil-soluble high carbon polar modified polymer hydrophilicgroup with which the at least two amine groups of the polyamine willreact. However, once the nature of the corresponding reactive groups isknown, their reaction with the at least two amine groups of thepolyamine will proceed according to known chemistry principles usingknown catalysts.

According to other preferred embodiments of the present invention, thereaction product is prepared without using a catalyst. Such preparationmethods will generally result in an incomplete reaction (full conversionof reactive products does not occur). However, such incompleteconversion of reactants may not be undesirable and, in fact, may bedesired under certain circumstances. For example, in formulatingcosmetic products, complete conversion of reactants may not be necessaryand, to the contrary, may be undesirable because of the time and expenseassociated with achieving complete conversion. Whereas completeconversion may occur after a couple of hours in the presence of acatalyst, incomplete conversion occurs if the reaction proceeds morequickly and/or without catalyst. The reaction product resulting fromsuch incomplete reactions are perfectly acceptable for many uses (suchas inclusion into cosmetic products).

According to preferred embodiments, the oil carrier comprises volatileand/or non-volatile oils. Such oils can be any acceptable oil includingbut not limited to silicone oils and/or hydrocarbon oils.

According to preferred embodiments, the oil carrier comprises one ormore volatile silicone oils. Examples of such volatile silicone oilsinclude linear or cyclic silicone oils having a viscosity at roomtemperature less than or equal to 6 cSt and having from 2 to 7 siliconatoms, these silicones being optionally substituted with alkyl or alkoxygroups of 1 to 10 carbon atoms. Specific oils that may be used in theinvention include octamethyltetrasiloxane, decamethylcyclopentasiloxane,dodecamethylcyclohexasiloxane, heptamethyloctyltrisiloxane,hexamethyldisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxaneand their mixtures. Other volatile oils which may be used include KF 96Aof 6 cSt viscosity, a commercial product from Shin Etsu having a flashpoint of 94° C. Preferably, the volatile silicone oils have a flashpoint of at least 40° C.

Non-limiting examples of volatile silicone oils are listed in Table 1below.

TABLE 1 Flash Point Viscosity Compound (° C.) (cSt) Octyltrimethicone 931.2 Hexyltrimethicone 79 1.2 Decamethylcyclopentasiloxane 72 4.2(cyclopentasiloxane or D5) Octamethylcyclotetrasiloxane 55 2.5(cyclotetradimethylsiloxane or D4) Dodecamethylcyclohexasiloxane (D6) 937 Decamethyltetrasiloxane(L4) 63 1.7 KF-96 A from Shin Etsu 94 6 PDMS(polydimethylsiloxane) DC 200 56 1.5 (1.5 cSt) from Dow Corning PDMS DC200 (2 cSt) from Dow Corning 87 2

Further, a volatile linear silicone oil may be employed in the presentinvention. Suitable volatile linear silicone oils include thosedescribed in U.S. Pat. No. 6,338,839 and WO03/042221, the contents ofwhich are incorporated herein by reference. In one embodiment thevolatile linear silicone oil is decamethyltetrasiloxane. In anotherembodiment, the decamethyltetrasiloxane is further combined with anothersolvent that is more volatile than decamethyltetrasiloxane.

According to other preferred embodiments, the oil carrier comprises oneor more non-silicone volatile oils and may be selected from volatilehydrocarbon oils, volatile esters and volatile ethers. Examples of suchvolatile non-silicone oils include, but are not limited to, volatilehydrocarbon oils having from 8 to 16 carbon atoms and their mixtures andin particular branched C₈ to C₁₆ alkanes such as C₈ to C₁₆ isoalkanes(also known as isoparaffins), isododecane, isodecane, and for example,the oils sold under the trade names of Isopar or Permethyl. Preferably,the volatile non-silicone oils have a flash point of at least 40° C.

Non-limiting examples of volatile non-silicone volatile oils are givenin Table 2 below.

TABLE 2 Compound Flash Point (° C.) Isododecane 43 Propylene glycoln-butyl ether 60 Ethyl 3-ethoxypropionate 58 Propylene glycolmethylether acetate 46 Isopar L (isoparaffin C₁₁-C₁₃) 62 Isopar H(isoparaffin C₁₁-C₁₂) 56

The volatility of the solvents/oils can be determined using theevaporation speed as set forth in U.S. Pat. No. 6,338,839, the contentsof which are incorporated by reference herein.

According to preferred embodiments of the present invention, the oilcarrier comprises at least one non-volatile oil. Examples ofnon-volatile oils that may be used in the present invention include, butare not limited to, polar oils such as:

-   -   hydrocarbon-based plant oils with a high triglyceride content        consisting of fatty acid esters of glycerol, the fatty acids of        which may have varied chain lengths, these chains possibly being        linear or branched, and saturated or unsaturated; these oils are        especially wheat germ oil, corn oil, sunflower oil, karite        butter, castor oil, sweet almond oil, macadamia oil, apricot        oil, soybean oil, rapeseed oil, cottonseed oil, alfalfa oil,        poppy oil, pumpkin oil, sesame seed oil, marrow oil, avocado        oil, hazelnut oil, grape seed oil, blackcurrant seed oil,        evening primrose oil, millet oil, barley oil, quinoa oil, olive        oil, rye oil, safflower oil, candlenut oil, passion flower oil        or musk rose oil; or caprylic/capric acid triglycerides, for        instance those sold by the company Stearineries Dubois or those        sold under the names Miglyol 810, 812 and 818 by the company        Dynamit Nobel;    -   synthetic oils or esters of formula R₅COOR₆ in which R₅        represents a linear or branched higher fatty acid residue        containing from 1 to 40 carbon atoms, including from 7 to 19        carbon atoms, and R₆ represents a branched hydrocarbon-based        chain containing from 1 to 40 carbon atoms, including from 3 to        20 carbon atoms, with R₆+R₇≧10, such as, for example, Purcellin        oil (cetostearyl octanoate), isononyl isononanoate, C₁₂ to C₁₅        alkyl benzoate, isopropyl myristate, 2-ethylhexyl palmitate, and        octanoates, decanoates or ricinoleates of alcohols or of        polyalcohols; hydroxylated esters, for instance isostearyl        lactate or diisostearyl malate; and pentaerythritol esters;    -   synthetic ethers containing from 10 to 40 carbon atoms;    -   C₈ to C₂₆ fatty alcohols, for instance oleyl alcohol; and    -   mixtures thereof.

Further, examples of non-volatile oils that may be used in the presentinvention include, but are not limited to, non-polar oils such asbranched and unbranched hydrocarbons and hydrocarbon waxes includingpolyolefins, in particular Vaseline (petrolatum), paraffin oil,squalane, squalene, hydrogenated polyisobutene, hydrogenated polydecene,polybutene, mineral oil, pentahydrosqualene, and mixtures thereof.

According to preferred embodiments of the present invention, the oilcarrier(s), the aqueous carrier, or two or more of these comprise adesired agent to be incorporated within the reaction product. Thedesired agent can be, for example, any colorant (pigment, dye, etc.),any pharmaceutically or cosmetically active agent, or any film formingagent known in the art. Such a desired agent can be incorporated intothe reaction product of the present invention and can be active duringsubsequent use of a composition comprising the reaction product. Forexample, a cosmetic makeup composition or a paint composition comprisingcolorant within the reaction product can provide colorant and/or filmforming agent to a substrate (skin, lips, wall, frame, etc.) during useto provide the substrate with the desired film and/or color. Similarly,a pharmaceutical or cosmetic composition comprising a pharmaceuticallyactive agent can provide such active agent to the patient or consumerupon use (for example, a transdermal patch containing the reactionproduct of the present invention within which is a pharmaceutically orcosmetically active agent, or a tablet or capsule containing the samereaction product/active agent combination).

Acceptable colorants include pigments, dyes, such as liposoluble dyes,nacreous pigments, and pearling agents.

Representative liposoluble dyes which may be used according to thepresent invention include Sudan Red, DC Red 17, DC Green 6, β-carotene,soybean oil, Sudan Brown, DC Yellow 11, DC Violet 2, DC Orange 5,annatto, and quinoline yellow.

Representative nacreous pigments include white nacreous pigments such asmica coated with titanium or with bismuth oxychloride, colored nacreouspigments such as titanium mica with iron oxides, titanium mica withferric blue or chromium oxide, titanium mica with an organic pigmentchosen from those mentioned above, and nacreous pigments based onbismuth oxychloride.

Representative pigments include white, colored, inorganic, organic,polymeric, nonpolymeric, coated and uncoated pigments. Representativeexamples of mineral pigments include titanium dioxide, optionallysurface-treated, zirconium oxide, zinc oxide, cerium oxide, iron oxides,chromium oxides, manganese violet, ultramarine blue, chromium hydrate,and ferric blue. Representative examples of organic pigments includecarbon black, pigments of D & C type, and lakes based on cochinealcarmine, barium,

Acceptable film forming agents and/or rheological agents are known inthe art and include, but are not limited to, those disclosed in U.S.patent application publication no. 2004/0170586, the entire contents ofwhich is hereby incorporated by reference.

Non-limiting representative examples of acceptable filmforming/rheolgocial agents include silicone resins such as, for example,MQ resins (for example, trimethylsiloxysilicates), T-propylsilsesquioxanes and MK resins (for example, polymethylsilsesquioxanes),silicone esters such as those disclosed in U.S. Pat. Nos. 6,045,782,5,334,737, and 4,725,658, the disclosures of which are herebyincorporated by reference, polymers comprising a backbone chosen fromvinyl polymers, methacrylic polymers, and acrylic polymers and at leastone chain chosen from pendant siloxane groups and pendant fluorochemicalgroups such as those disclosed in U.S. Pat. Nos. 5,209,924, 4,693,935,4,981,903, 4,981,902, and 4,972,037, and WO 01/32737, the disclosures ofwhich are hereby incorporated by reference, polymers such as thosedescribed in U.S. Pat. No. 5,468,477, the disclosure of which is herebyincorporated by reference (a non-limiting example of such polymers ispoly(dimethylsiloxane)-g-poly(isobutyl methacrylate), which iscommercially available from 3M Company under the tradename VS 70 IBM).

Suitable examples of acceptable liposoluble polymers include, but arenot limited to, polyalkylenes, polyvinylpyrrolidone (PVP) orvinylpyrrolidone (VP) homopolymers or copolymers, copolymers of a C₂ toC₃₀, such as C₃ to C₂₂ alkene, and combinations thereof. As specificexamples of VP copolymers which can be used in the invention, mentionmay be made of VP/vinyl acetate, VP/ethyl methacrylate, butylatedpolyvinylpyrrolidone (PVP), VP/ethyl methacrylate/methacrylic acid,VP/eicosene, VP/hexadecene, VP/triacontene, VP/styrene or VP/acrylicacid/lauryl methacrylate copolymer.

One type of block copolymer which may be employed in the compositions ofthe present invention is a thermoplastic elastomer. The hard segments ofthe thermoplastic elastomer typically comprise vinyl monomers in varyingamounts. Examples of suitable vinyl monomers include, but are notlimited to, styrene, methacrylate, acrylate, vinyl ester, vinyl ether,vinyl acetate, and the like.

The soft segments of the thermoplastic elastomer typically compriseolefin polymers and/or copolymers which may be saturated, unsaturated,or combinations thereof. Suitable olefin copolymers may include, but arenot limited to, ethylene/propylene copolymers, ethylene/butylenecopolymers, propylene/butylene copolymers, polybutylene, polyisoprene,polymers of hydrogenated butanes and isoprenes, and mixtures thereof.

Thermoplastic elastomers useful in the present invention include blockcopolymers e.g., di-block, tri-block, multi-block, radial and star blockcopolymers, and mixtures and blends thereof. A di-block thermoplasticelastomer is usually defined as an A-B type or a hard segment (A)followed by a soft segment (B) in sequence. A tri-block is usuallydefined as an A-B-A type copolymer or a ratio of one hard, one soft, andone hard segment. Multi-block or radial block or star blockthermoplastic elastomers usually contain any combination of hard andsoft segments, provided that the elastomers possess both hard and softcharacteristics.

In preferred embodiments, the thermoplastic elastomer of the presentinvention may be chosen from the class of Kraton™ rubbers (ShellChemical Company) or from similar thermoplastic elastomers. Kraton™rubbers are thermoplastic elastomers in which the polymer chainscomprise a di-block, tri-block, multi-block or radial or star blockconfiguration or numerous mixtures thereof. The Kraton™ tri-blockrubbers have polystyrene (hard) segments on each end of a rubber (soft)segment, while the Kraton™ di-block rubbers have a polystyrene (hard)segment attached to a rubber (soft) segment. The Kraton™ radial or starconfiguration may be a four-point or other multipoint star made ofrubber with a polystyrene segment attached to each end of a rubbersegment. The configuration of each of the Kraton™ rubbers forms separatepolystyrene and rubber domains.

Each molecule of Kraton™ rubber is said to comprise block segments ofstyrene monomer units and rubber monomer and/or co-monomer units. Themost common structure for the Kraton™ triblock copolymer is the linearA-B-A block type styrene-butadiene-styrene, styrene-isoprene-styrene,styrene-ethylenepropylene-styrene, or styrene-ethylenebutylene-styrene.The Kraton™ di-block is preferably the AB block type such asstyrene-ethylenepropylene, styrene-ethylenebutylene, styrene-butadiene,or styrene-isoprene. The Kraton™ rubber configuration is well known inthe art and any block copolymer elastomer with a similar configurationis within the practice of the invention. Other block copolymers are soldunder the tradename Septon (which represent elastomers known as SEEPS,sold by Kurary, Co., Ltd) and those sold by Exxon Dow under thetradename Vector™.

Other thermoplastic elastomers useful in the present invention includethose block copolymer elastomers comprising astyrene-butylene/ethylene-styrene copolymer (tri-block), anethylene/propylene-styrene copolymer (radial or star block) or a mixtureor blend of the two. (Some manufacturers refer to block copolymers ashydrogenated block copolymers, e.g. hydrogenatedstyrene-butylene/ethylene-styrene copolymer (tri-block)).

Acceptable film forming/rheological agents also include water solublepolymers such as, for example, high molecular weight crosslinkedhomopolymers of acrylic acid, and Acrylates/C10-30 Alkyl AcrylateCrosspolymer, such as the Carbopol® and Pemulen®; anionic acrylatepolymers such as Salcare® AST and cationic acrylate polymers such asSalcare® SC96; acrylamidopropylttrimonium chloride/acrylamide;hydroxyethyl methacrylate polymers, Steareth-10 Allyl Ether/AcrylateCopolymer; Acrylates/Beheneth-25 Metacrylate Copolymer, known as Aculyn®28; glyceryl polymethacrylate, Acrylates/Steareth-20 MethacrylateCopolymer; bentonite; gums such as alginates, carrageenans, gum acacia,gum arabic, gum ghatti, gum karaya, gum tragacanth, guar gum; guarhydroxypropyltrimonium chloride, xanthan gum or gellan gum; cellulosederivatives such as sodium carboxymethyl cellulose, hydroxyethylcellulose, hydroxymethyl carboxyethyl cellulose, hydroxymethylcarboxypropyl cellulose, ethyl cellulose, sulfated cellulose,hydroxypropyl cellulose, methyl cellulose, hydroxypropylmethylcellulose, microcrystalline cellulose; agar; pectin; gelatin; starch andits derivatives; chitosan and its derivatives such as hydroxyethylchitosan; polyvinyl alcohol, PVM/MA copolymer, PVM/MA decadienecrosspolymer, poly(ethylene oxide) based thickeners, sodium carbomer,and mixtures thereof.

According to preferred embodiments of the present invention,compositions of the present invention can comprise substantial amountsof water. Preferably, compositions of the present invention comprisefrom about 5% to about 50% water, more preferably from about 15% toabout 45% water, and more preferably from about 25% to about 40% waterby weight with respect to the total weight of the composition, includingall ranges and subranges therebetween. According to particularlypreferred embodiments, compositions comprising the reaction product ofthe present invention and at least 25% water are solid compositions.Such solid compositions are preferably in the form of a stick (forexample, a lipstick or a stick foundation).

Compositions of the present invention can optionally further compriseany additive usually used in the field(s) under consideration. Forexample, dispersants such as poly(12-hydroxystearic acid), antioxidants,essential oils, sunscreens, preserving agents, fragrances, fillers,neutralizing agents, cosmetic and dermatological active agents such as,for example, emollients, moisturizers, vitamins, essential fatty acids,surfactants, silicone elastomers, pasty compounds, viscosity increasingagents such as waxes or liposoluble/lipodispersible polymers, andmixtures thereof can be added. A non-exhaustive listing of suchingredients can be found in U.S. patent application publication no.2004/0170586, the entire contents of which are hereby incorporated byreference. Further examples of suitable additional components can befound in the other references which have been incorporated by referencein this application. Still further examples of such additionalingredients may be found in the International Cosmetic IngredientDictionary and Handbook (9^(th) ed. 2002).

One particularly preferred embodiment of the present invention is anemulsion which is substantially free of surfactant (that is, less than3% of surfactant), essentially free of surfactant (that is, less than 2%surfactant), or free of surfactant (that is, less than 0.5% surfactant).

Another particularly preferred embodiment of the present invention is acomposition which contains so little elastomer that the presence of suchelastomer not affect the cosmetic properties of the composition.Preferably, the compositions are substantially free of such elastomers(i.e., contain less than about 0.5% elastomer), essentially free of suchelastomers (i.e., contain less than about 0.25% elastomer) or free ofsuch elastomer (i.e., contain no elastomer).

According to other embodiments of the present invention, thecompositions of the present invention are anhydrous. By “anhydrous,” itis meant that the composition contains substantially no water (that is,less than about 5% by weight of the composition of water).

According to other preferred embodiments, methods of treating, caringfor and/or enhancing the appearance of keratinous material by applyingcompositions of the present invention to the keratinous material in anamount sufficient to treat, care for and/or enhance the appearance ofthe keratinous material are provided. In accordance with these precedingpreferred embodiments, the compositions of the present inventioncomprising at least one polyol having at least two hydroxyl groups andat least one reaction product of at least one Oil-soluble high carbonpolar modified polymer and at least one polyamine are applied topicallyto the desired area of the keratin material in an amount sufficient totreat, care for and/or enhance the appearance of the keratinousmaterial. The compositions may be applied to the desired area as needed,preferably once or twice daily, more preferably once daily and thenpreferably allowed to dry before subjecting to contact such as withclothing or other objects (for example, a glass or a topcoat).Preferably, the composition is allowed to dry for about 1 minute orless, more preferably for about 45 seconds or less. The composition ispreferably applied to the desired area that is dry or has been driedprior to application, or to which a basecoat has been previouslyapplied.

According to a preferred embodiment of the present invention,compositions having improved cosmetic properties such as, for example,improved waterproof characteristics, improved feel upon application (forexample, texture, reduced drag or tackiness), increased anti-smudgingproperties, shine/color characteristics and/or increased long wearproperties are provided.

According to other embodiments of the present invention, methods ofimproving the anti-smudging, waterproof, transfer-resistance and/or longwear properties of a composition, comprising adding at least one polyolhaving at least two hydroxyl groups and at least one reaction product ofat least one Oil-soluble high carbon polar modified polymer and at leastone polyamine to the composition are provided.

Unless otherwise indicated, all numbers expressing quantities ofingredients, reaction conditions, and so forth used in the specificationand claims are to be understood as being modified in all instances bythe term “about.” Accordingly, unless indicated to the contrary, thenumerical parameters set forth in the following specification andattached claims are approximations that may vary depending upon thedesired properties sought to be obtained by the present invention.

Notwithstanding that the numerical ranges and parameters setting forththe broad scope of the invention are approximations, the numericalvalues set forth in the specific examples are reported as precisely aspossible. Any numerical value, however, inherently contain certainerrors necessarily resulting from the standard deviation found in theirrespective measurements. The following examples are intended toillustrate the invention without limiting the scope as a result. Thepercentages are given on a weight basis.

EXAMPLE 1 Lipstick

Phase Chemical Name % wt/wt A Octododecanol 10.50% A Octyldodecyl 10.00%Neopantanoate A HYDROGENATED 20.35% POLYISOBUTENE A POLYBUTENE 5.00% AIsohexadecane 3.00% A Tricaprylin 6.58% B C26-C28 Polar Modified 7.00%Wax B Polyethylene 400 4.00% B Polyethylene 500 4.00% B Ozokerite 0.50%B VP/Eicosene Copolymer 3.00% B Color Pigments and Pearls 7.07% CDeionized Water 15.00% C PEI-35 0.25% C Preservatives 0.75% C Glycerin3.00%Procedure

-   -   1. Phase A materials were added to a suitable size beaker A and        heated to 95 Celsius degrees.    -   2. When mixture was uniform phase B materials were added and        heated to 95 Celsius degrees.    -   3. When enough solids had melted, the contents were mixed with        moderate speed until all solids had melted at 95 Celsius        degrees.    -   4. The temperature was slightly lowered to 85 Celsius degrees.    -   5. The contents of main beaker A were transferred to a Silverson        mixer for emulsification while maintaining the temperature at        85-90 Celsius degrees.    -   6. In a separate beaker 2, phase C materials were added and        mixed and heated to 85 Celsius degrees.    -   7. The contents of side beaker B were added dropwise into the        beaker A while emulsifying at 9000 rpm under the Silverson mixer        for 30 minutes. Afterward, the emulsification speed was lowered        to 2000 rpm for 5 minutes.    -   8. The contents were poured into lipstick molds at 80 Celsius        degrees.    -   9. The lipstick in molds was placed in a cooling tunnel for 15        minutes at −10 Celsius degrees. Once cooled, the lipstick in        molds were removed from the cooling tunnel to equilibrate to 25        Celsius degrees and removed from the molds after lipsticks had        thawed to 25 Celsius degrees.

What is claimed is:
 1. A composition comprising: water; at least onehyperbranched polyol having at least two hydroxyl groups; and at leastone water-insoluble half acid and half amide crosslinked reactionproduct of at least one oil-soluble high carbon polar modified polymerand at least one polyamine, wherein the at least one oil-soluble highcarbon polar modified polymer comprises at least one C24-C38 monomer andis modified with at least one hydrophilic unit, and has a weight-averagemolecular weight of less than or equal to 30,000 g/mol and acrystallinity of 8% to 60%, and wherein the reaction product forms amatrix capable of entrapping water, the composition is in the form of anemulsion, and water is entrapped within the matrix.
 2. The compositionof claim 1, further comprising at least one colorant.
 3. The compositionof claim 1, wherein the at least one oil-soluble high carbon polarmodified polymer comprises maleic anhydride units.
 4. The composition ofclaim 1, wherein the composition comprises water in an amount rangingfrom about 15% to about 50% by weight with respect to the weight of thecomposition.
 5. The composition of claim 1, wherein the composition issolid.
 6. The composition of claim 5, wherein the composition is alipstick or a stick foundation.
 7. The composition of claim 1, whereinthe at least one polyamine is a branched polyalkyleneimine.
 8. Thecomposition of claim 1, wherein the polyamine is present in an amount offrom about 0.05 to about 20% by weight, based on the weight of thecomposition.
 9. The composition of claim 1, wherein the oil-soluble highcarbon polar modified polymer is present in an amount of from about 1%to about 20% by weight, based on the weight of the composition.
 10. Thecomposition of claim 1, wherein the hyperbranched polyol has a hydroxylnumber between 100 and
 200. 11. The composition of claim 1, wherein thehyperbranched polyol has a viscosity between 3,000 and 6,000 cps at 90°F.
 12. The composition of claim 1, wherein the hyperbranched polyol ispresent in an amount of from about 0.1 to about 15% by weight, based onthe weight of the composition.
 13. The composition of claim 1, whereinthe weight-average molecular weight of the oil-soluble high carbon polarmodified polymer is from 500 to 10,000 g/mol.
 14. The composition ofclaim 1, wherein the oil-soluble high carbon polar modified polymercomprises at least one C26-C28 monomer.
 15. The composition of claim 1,wherein the oil-soluble high carbon polar modified polymer has fromabout 5% to about 30% hydrophilic units by weight with respect to theweight of the oil-soluble high carbon polar modified polymer.
 16. Thecomposition of claim 1, wherein the oil-soluble high carbon polarmodified polymer has from about 10% to about 25% hydrophilic units byweight with respect to the weight of the oil-soluble high carbon polarmodified polymer.
 17. The composition of claim 1, wherein theoil-soluble high carbon polar modified polymer has from about 5% toabout 30% maleic anhydride units by weight with respect to the weight ofthe oil-soluble high carbon polar modified polymer.
 18. The compositionof claim 1, wherein the oil-soluble high carbon polar modified polymerhas from about 10% to about 25% maleic anhydride units by weight withrespect to the weight of the oil-soluble high carbon polar modifiedpolymer.
 19. The composition of claim 1, wherein the at least onepolyamine is polyethyleneimine.
 20. The composition of claim 1, whereinthe composition comprises water in an amount ranging from about 25% toabout 50% by weight with respect to the weight of the composition.